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| | Hexetidine Basic information |
| Product Name: | Hexetidine | | Synonyms: | 1,3-bis(2-ethylhexyl)hexahydro-5-methyl-5-pyrimidinamin;1,3-bis(2-ethylhexyl)hexahydro-5-methyl-5-Pyrimidinamine;hexetidine,5-amino-1,3-bis(2-ethylhexyl)hexahydro-5-methylpyrimidine;hexetidine,mixtureofstereoisomers;5-AMINO-1,3-BIS(2-ETHYLHEXYL)HEXAHYDRO-5-METHYLPYRIMIDINE;HEXETIDINE;LABOTEST-BB LT00134693;5-Amino-1,3-bis(2-ethylhexyl)hexahydro-5-methylpyrimidine, mix of diastereomers | | CAS: | 141-94-6 | | MF: | C21H45N3 | | MW: | 339.6 | | EINECS: | 205-513-5 | | Product Categories: | STERISIL | | Mol File: | 141-94-6.mol |  |
| | Hexetidine Chemical Properties |
| Provider | Language |
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ALFA
| English |
| | Hexetidine Usage And Synthesis |
| Chemical Properties | Liquid.Soluble in methanol, benzene, and petroleum
ether; insoluble in water. | | Chemical Properties | Hexetidine is a colorless or faint yellow-colored oily liquid with a
characteristic amine odor. | | Originator | Sterisil,Warner Lambert,US,1956 | | Uses | Hexetidine, mixture of stereoisomers is an antibacterial and antifungal agent. Used in plant-derived composite antimicrobial agent and application thereof in cosmetic. | | Uses | Involved in studies:
- To identify pure liquid salt forms of aspirin
- Of alkyl based selective displacers for protein purification via ion exchange chromatography
- Of the in vivo application of models for testing drugs against nonreplicating Mycobacterium tuberculosis
- Nutrient-sensitized screening for drugs that shift the energy metabolism from mitochondrial respiration to glycolysis
- Inhibition of angiogensis
- Screening antimalarial drugs
| | Uses | Fungicide, bactericide, algicide, antistatic agent
for synthetics, insect repellent, medicine (antifungal
agent). | | Production Methods | Hexetidine is prepared by hydrogenation under pressure of 1,3-
bis(2-ethylhexyl)-5-methyl-4-nitrohexahydropyriminine at 100°C
using Raney nickel as a catalyst. | | Definition | ChEBI: 1,3-bis(2-ethylhexyl)-5-methyl-1,3-diazinan-5-amine is an organonitrogen heterocyclic compound and an organic heteromonocyclic compound. | | Manufacturing Process | Nitroethane and formaldehyde are first reacted to give 2-methyl-2-nitro-1,3-
propanediol. This is reacted with 2-ethylhexylamine and formaldehyde to give
5-nitro-1,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine.
To a hydrogenation apparatus containing 500 ml of methanol and 10 g of
Raney nickel catalyst were continuously added over a period of one hour, 240
g of 5-nitro-1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine. During the
one-hour period, the resulting mixture was hydrogenated at approximately
1,000 pounds per square inch utilizing room temperature as the initial
temperature and gradually increasing the temperature to about 70°C. At the
end of the one-hour period, hydrogenation was stopped. The reaction mixture
was first filtered to remove the catalyst and was then distilled at atmospheric
pressure at a temperature of 70°C to remove methanol. 197.5 g of 5-amino-
1,3-bis(2-ethylhexyl)-5-methylhexahydropyrimidine were collected. | | Therapeutic Function | Antifungal | | General Description | The effectiveness of a hexetidine mouthwash in reducing supragingival plaque and gingival inflammation has been examined. | | Hazard | Combustible. | | Pharmaceutical Applications | Hexetidine is used as an antimicrobial preservative in cosmetics and
nonparenteral pharmaceutical formulations. Therapeutically, hexetidine
is mainly used as a 0.1% w/v solution in mouthwash
formulations for the prevention and treatment of minor local
infections, gingivitis, and mouth ulcers. | | Safety | Hexetidine is mainly used in mouthwashes as a bactericidal and
fungicidal antiseptic. It is also used as an antimicrobial preservative
and is generally regarded as a relatively nontoxic and nonirritant
material at concentrations up to 0.1% w/v. Allergic contact
dermatitis and altered olfactory and taste perception have
occasionally been reported. Hexetidine is toxic when administered
intravenously.
Solutions of hexetidine in oil at concentrations of 5–10% w/v
cause strong primary irritations without sensitization in humans.
Long-term toxicological studies of up to 0.1% w/w of hexetidine in
food for 1 year do not show any toxic effect. Fetotoxicity,
embryotoxicity, and teratogenicity studies in rats of doses up to
50 mg/kg/day exhibit no sign of toxicity.
LD100 (cat, IV): 5–20 mg/kg
LD50 (dog, oral): 1.60 g/kg
LD50 (mouse, IP): 0.142 g/kg
LD50 (mouse, oral): 1.52 g/kg
LD50 (rat, oral): 0.61–1.43 g/kg | | storage | Hexetidine is stable and should be stored in a well-closed container
in a cool, dry place. Brass and copper equipment should not be used
for the handling or storage of hexetidine. | | Incompatibilities | Hexetidine is incompatible with strong oxidizing agents. Salts are
formed with mineral and organic acids; strong acids cause opening
of the hexahydropyrimidine ring, releasing formaldehyde. | | Regulatory Status | Included in nonparenteral formulations licensed in Europe. |
| | Hexetidine Preparation Products And Raw materials |
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